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Throughout his long career, in New York, Silicon Valley and LA, Jason Calacanis has made a good number of friends, but a better number of enemies. At PandoMonthly, Calacanis and Sarah Lacy delved into his personal history and he revealed where his infamous fighting side came from.

Calacanis grew up in in Brooklyn, from a middling income family. The expectation was that he’d become a cop, which is exactly what his little brother did. In fact, he even took the policeman’s test. But instead of becoming a cop he got into Fordham, right around the time of what Calacanis calls “the second most traumatic of his life.” The most traumatic was 9/11.

His father, who owned a restaurant, evaded his taxes. And one day during the summer of ’88, the feds arrived with shotguns to repossess the restaurant. “He lost everything and never he never recovered from it. That was the end of his entrepreneurial career,” Calacanis says. “When you see your dad lose his business and get crushed, it changes a boy.”

Calacanis points to that traumatic event as the defining turning point for him as an entrepreneur. He had to pay his own way through college, so he worked a few jobs simultaneously while finishing his degree. “I had to win, I could never let the bastards take me down like they took my dad down,” Calacanis says. It put a fight in him that was superhuman. He called it a resiliency and a fire that he didn’t know he had. But he quickly admitted, “It served me very well, until it didn’t… I did have a drive that was so strong people probably looked at me and said why Jason why are you pushing so hard?”

He believes the fire is what made him who he is, and that celebrating that aspect has made him a great entrepreneur.

“The best moments in my career have been the darkest,” Calacanis said, insisting that he’s gotten the most enjoyment out of the toughest times.

“It seems perverse, in a way,” Calacanis said.

“It is fucked up,” Lacy agreed.

“I always felt that when I got punched in the face and had blood in my mouth that I was at my best.”

Despite that, eventually he got tired of fighting. “A large part of entrepreneurship, you’re so used to fighting for a long time that sometimes you’re just a fighter,” Calacanis said. “If you fight your whole life you don’t really know there’s some other mode.”

He went on to explain that he spent his first ten years in his career fighting, but he’s tried to spend the last ten years as a leader supporting people. In fact, he says he doesn’t enjoy the fight as much as he enjoys building teams. Like Maslow’s Hierarchy of Needs, now he’s fulfilling higher purpose motivations than survival.

[Photo by Rebecca Aranda for Pandodaily]